


An Impossibly Troublesome Feat

by raebil



Category: Naruto
Genre: Canon Rewrite, Canon-Typical Violence, Gen, M/M, Slow Burn, Uchiha Itachi Deserved Better
Language: English
Status: In-Progress
Published: 2020-10-28
Updated: 2021-02-14
Packaged: 2021-03-08 17:08:16
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 14,900
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27250216
Author URL: https://archiveofourown.org/users/raebil/pseuds/raebil
Summary: Shikamaru had been wounded, facing certain death, and was sure to not make it back to Konoha alive. That was, until he had an unlikely encounter with Itachi. Despite the rumors, there was compassion there that most men of the shinobi world could never muster, and Shikamaru finds himself nearly obsessed with unlocking the puzzle. He had to find out exactly who Itachi Uchiha truly was.(AKA: Rare/crack ship in which I told myself that Itachi and Shikamaru could never become lovers, until I decided I would try my damnedest to make it a reality)
Relationships: Nara Shikamaru & Uchiha Itachi, Nara Shikamaru/Uchiha Itachi
Comments: 15
Kudos: 50





	1. A Fated Encounter

**Author's Note:**

> Hey, thanks for checking out my brain worm plot I conjured up. This story takes place after Gaara had his jinchuriki extracted, maybe a month or two after that, at least that is what I am going with. Don't be surprised if this steers into completely not canon, I am just going where the story takes me.
> 
> Don't ask me why I thought that Shikamaru and Itachi could even become friends to lovers, this is the most unlikely pair I have ever thought of. Some drama and angst are to brew on the horizon for sure, but for now take an awkward first encounter.

Shikamaru knew what it was like to be injured, knew how it felt to be flung and beaten as enemy shinobi attacked him, but he never anticipated that it would kill him. There was always the faint knowledge in the back of his mind, that he could in fact die, but perhaps it was his own ego that thought he could outmaneuver anyone who crossed his path. If he could not do it in physical combat, his mind function would always be there to save him. The odds of an ambush as he was retreating from his mission to help guide a nobleman to Suna were always there, as he knew the odds of anything happening at any time were, but his mind had placed it so low on the likeliness scale that he didn’t know what happened until he was already retreating with a large gash in his side.

He had not thought he was important enough, he presumed, knowing that he was of Konoha and that immediately made him a threat to rogue shinobi, but he was not like Kakashi or Naruto. His name did not precede him, he did not get recognized easily amongst the streets of allied villages. Shikamaru was simply as plain as they came, his brain the only thing that even made him noteworthy when it came to strategy and warfare. As he wandered the desert for some sort of shelter as the sun started to set in the distance, he knew he would be dead by sunrise if he could not aid his wounds. If the blood loss did not get him first, the frigged night in the Land of Wind would certainly get to him. All his mind could provide to him was that it was awfully troublesome to keep moving when his side constantly screamed at him to cease movement.

If it had been his arm, that would have been preferred, because at least every step that was increasingly becoming more staggered would be more bearable than the fire radiating from his injury. Shikamaru knew he should be content with his injury, as he would be even more useless if he could not make any hand signs, though as the shadows became ever longer and darkness was soon setting on the desert, he knew that he wouldn’t be of much use either way. He had considered multiple times as he wandered the vastness of the desert that he should just give up, that it was obvious that his defeat was imminent. The rogue shinobi who had attacked him would practically cheer to know that they had successfully killed one of Konoha’s own, even if they had no idea who the Nara clan was. It was his own pride that kept him going, knowing that he could not allow those bastards the glee they would inevitably have to know he had fallen.

It was almost bittersweet when he came upon a gathering of trees a few kilometers away, knowing he was entering the Land of River, knowing he had made it out of the desert at last. Though, as he fumbled to carry himself as his flask jacket seemed to be dampened with too much blood, Shikamaru did not believe he could survive and make it much further. Clumsily, once inside the forest and unable to move much more, he leaned against one of the trees and let out another staggered breath. So troublesome, his mind repeated to him as if some sort of broken record, as he worked the clasps of his jacket off to expose the wound to investigate further. It was deep and slowly oozing blood, which was comforting that his body was trying to aid in the repair, and the gash ran from close to his navel to his left hip. He could only sigh with the knowledge that he should have taken Ino up on her offer to show him some rudimentary healing jutsu. Digging through his weapon pouch, he procured the measly amount of medicinal salve he had and rubbed it across the wound, hissing in pain as he nearly doubled over. That was about the extent of Shikamaru’s medical knowledge, he bitterly knew as he used a kunai to tear part of his pants to apply pressure. So long as he could make it to the Land of Fire, he knew his odds of being found would raise astronomically.

That was he thought, at least, until he felt a chakra signature nearby and all he could think was that was the end. Shikamaru was going to die by whoever was approaching him, and there was nothing he could do about it. Vaguely, his mind reeled at the knowledge he would never see his team again. He would never be allowed to see Ino or Choji or even the troublesome woman Temari. Asuma would never know where Shikamaru hid his cigarettes and could never scorn him for trying to have his sensei’s wellbeing in mind, even though Asuma himself never thought of his smokes being hid as such. His mom would be pissed, and he realized that a part of him would miss the constant nagging of the woman, and his old man would undoubtedly be equally as torn at the knowledge that his son passed before him. Even if they were shinobi and dying was a natural part of the job, he knew that parents losing their child before they died was haunting. His mind wondered if Naruto would ever become the Hokage like he yearned for since they were children, wondered if Hinata would get the courage to ask the oblivious blonde knucklehead out, and he wondered if Sasuke would ever return to the village that missed him.

He did not have long to ponder most of these ideas, as the chakra of whomever was heading towards him was becoming dangerously close to him, and he thought it was troublesome. Still, he held his kunai in front of him, preparing to fight even if it would inevitably be in vain. Shikamaru thought it was another rogue shinobi who was plotting to finish what the ones before had started, but instead he came face to face with blood red eyes. His back straightened slightly, ignoring the way his wound sent pain throughout him, and he wondered if it was Sasuke before him. That was not right, though, and it shook him further to see the long black hair tied into a long ponytail, the exaggerated tear ducts, and the overall menacing appearance of the man before him. Itachi Uchiha, the S-ranked missing shinobi who was one of many top priority men to capture and bring back to Konoha. His jaw clenched in preparation for a fight, knowing that there was no way in hell that someone of the Uchiha’s caliber would simply pass on murdering more of the Konoha population.

The tension was thick in the air, as Shikamaru’s shaky hand tried to grasp confidently at his kunai, and it felt like years before either shinobi moved. He anticipated Itachi would attempt to attack him, would put him into a genjutsu and torture him as was his forte, or he would simply be impaled by one of the many weapons undoubtedly held on the missing-nin’s person. Shikamaru did not know if he was even breathing, too entranced by staring at Itachi’s shoes to make sure that the other could not trap him in the Sharingan that was activated. It was only during the silent air around them that he took note of the cloak that was normally on the Uchiha was not adorned, showing just how small and almost fragile the man’s body was. His eyes travelled up the expanse of his body to take note that he looked almost gaunt, knowing that if he were to dare a glance at Itachi’s face that perhaps he would see sunken cheekbones and sharper features than one would normally attribute to someone who was capable of killing their entire clan in one night. It was odd, to take note of something so pointless when he would not make it through the encounter. His odds of survival were about as good as they were when he was in the desert.

“You won’t make it through the night,” a cold voice said, Shikamaru attributed it to the Uchiha, and he didn’t think he had ever been this close to such a dastardly enemy of Konoha before. His mouth didn’t seem to want to cooperate, to even let out a quip about how Itachi only pointed out the obvious, and he could only watch in some shock as the other walked around the area to scour for something. Through his slightly dazed mind, he realized that the other was gathering wood, and that did not make sense. A time or two the other’s back was turned to him, and Shikamaru had to wonder if he was truly even a shinobi for not attempting to do anything to take down the other. Though, his own chakra reserves were nearly depleted, and the night sky made his shadow jutsu utterly useless, so all he could do was try to ascertain why the man was collecting wood in the dead of night. It was not until he saw Itachi positioning the wood to make a fire that he even realized what was going on. Was the missing-nin actually making a fire? For what reason? His eyebrows furrowed in confusion as the other made the signs for a fireball jutsu and lit the fire, because the fire was not big enough to burn Shikamaru’s flesh alive if that was the idea.

It wasn’t until the fire was built that Itachi even seemed to take note of Shikamaru again, and the Konoha shinobi refused to meet those dangerous eyes even if his curiosity to know what the other appeared to be thinking was tempting him. Then the enemy, the one person that was never supposed to do anything nice for Shikamaru or Konoha shinobi in general, took to sitting in front of the fire to make sure that it was properly going before procuring what appeared to be fish from the bag he held that Shikamaru’s injured mind didn’t take note of previously. Itachi went to work putting two fish near the fire, and it took far too long to realize that the other was cooking another fish for the wounded shinobi. An S-rank criminal was extending an olive branch, perhaps it was his way of saying that neither of them would attack the other, not necessarily that Shikamaru was in any place to aggravate a fight. Honestly, the fire’s embers and warmth were almost too good to pass up, and it was not as though the man before him was acting aggressive. It took him a few minutes before he silently took to sitting across from Itachi, the fire aiding in warming his frigged skin.

“What are we doing here, Uchiha?” The Nara spoke first, cursing his voice for not coming out as strong as he wanted it to. The stress he inflicted on his wound from traveling through the desert was certainly what he would blame on his compliance. His mind was screaming at him to retreat, to not humor a mass murderer who could easily destroy Shikamaru before he even knew he was bested, but he felt so horribly tired. Despite his better judgement, his eyes did steal a glance of the other’s face and upon further investigation he could surmise that the other was worse for wear. How odd, was his only thought, as it appeared that the Uchiha was not harmed in any meaningful way. Could it mean that it was an illness that caused the gaunt appearance of his cheekbones, or was it the aftermath of a particularly rough mission? Those red eyes were looking directly at him, and it caused a chill to run down his spine at the knowledge that he could be dead within minutes if he were to say the wrong thing, make the wrong move.

“We’re eating a meal in front of a fire,” was the blasé response he got, and it caused a flare of annoyance to overwhelm the original terror he felt. The few and far between times he had spoken or been around Sasuke, he pieced together that the air of cold calmness was a genetic trait of the Uchiha. When Shikamaru’s lack of response was evidently taken as a need for Itachi to explain further, an uncharacteristically somber expression appeared on the Sharingan user’s face. “I’ve grown tired.” It was a vague answer to a question that really held no reason to have that as a retort, and Shikamaru’s mind felt as though it was racing to piece together a rational reason why they were actually in the situation they were in. Itachi’s lack of assault could only mean that he was perhaps too weak to engage in any sort of confrontation, and if that were the case, then did that mean that he was truly ill? Most likely, it was impossible to get a medic to heal a missing-nin, and there was only so much that one could do for themselves if the illness were too strong.

“You’re aware I am a ninja from Konoha, the village you betrayed years ago, and have every capability of telling the Hokage of your whereabouts if I am to survive the night.”

“I am.”

The flippancy nearly took Shikamaru off guard, and for a moment he considered if it was simply the Uchiha’s pride that kept him so unaffected. If Konoha were to send shinobi to scope the area and try to capture the missing-nin, it was unlikely that they would survive. Itachi was far stronger than to be outsmarted by most of Konoha’s best, and even if there was an illness destroying his body. Just because his body was weakened did not mean that the Sharingan swirling in the other’s eyes was any worse for wear. However, the longer he sat and contemplated that response as a pale hand offered him the cooked fish, he came to the revelation that there was only acceptance in the man’s voice. As though he anticipated his actions would cause something like that, perhaps there was even misguided hope that shinobi would hunt him down within the Land of River. Unsure of how to approach the situation, unsure of what Shikamaru could even say for once, he took to taking bites out of the fish. There was no reason to believe them to be poisoned, not when he found that he could look into the other’s eyes and not be caught in a genjutsu. Prodding his injured side and feeling the pain radiate up his side was proof of that, as what he perceived in front of him did not change. So, it was no genjutsu being used, and he was actually being civil with the enemy.

“Do you have anything to gain from saving my life?” It was a question in the back of his mind, and even though his wounds had not been tended to other than his own rudimentary medical skills, he still knew that if he hadn’t been warmed by the fire and given food to gather his strength then he truly would have suffered. Itachi Uchiha was becoming more of an enigma than he already was to those not ranked to know of him more than quiet whispers and rumors. It was troublesome to know he was in the situation before him, even more troublesome that he was somewhat indebted to the Uchiha for actively showing some amount of compassion. Even if he were the enemy, his actions were not speaking of someone who was as merciless and horrifying as the rumored clan killer. Either that or his injury was becoming so prevalent that even his mind was heading towards delirium and he was actively becoming crazed enough to imagine something as unlikely as the situation before him.

“I have nothing to gain from helping you,” came the terrible response. It did not fit, nothing about the situation before him fit. Shikamaru’s mind reeled at knowing that this could potentially be a lie, or it could be that Itachi was truly acting out of compassion. Two strangers meeting by chance and simply helping each other out. Even if Itachi’s name preceded him, and everyone in the shinobi world knew of him, the same could not be said of the Nara heir. Sure, he had been the first of the rookie nine to be promoted to Chunin, but that was his only really reigning achievement. If he were more motivated, he could do so much more, but honestly Shikamaru was still teetering the line of even wanting to be a shinobi. Even despite his rank, he often wondered what would happen if he renounced his shinobi status. The clouds were not nearly as complicated as delicate politics and obviously kinder-than-originally-assumed Uchihas. “I’ve nothing to lose from helping you, either.”

Shikamaru assumed that was also correct, as it was not as though he was someone on the missing-nin group Akatsuki’s radar. He was simply a shinobi, an enemy shinobi, but there was no importance to him dying. Not to whatever goals the group held, as they obviously would rather capture Naruto or one of the other jinchuriki. There was the option that Shikamaru could take this moment to interrogate, to try to extract information from the man that sat calmly before him, but it was still a dangerous situation. The chance that Itachi would either strike him dead or vacate the premises was highly probable if he did attempt to pry, however, so all he could do was allow the somewhat stilted companionable silence to fill the air. Most of his curiosity and questions that filtered through his mind would only end in the Uchiha shutting him out, but that did not mean he could not at least attempt some amount of intelligence gathering.

“I was under the impression that you would be stronger looking,” and honestly provoking wasn’t the smartest idea when Shikamaru was not strong enough to flee the area if a fight were to occur, but it was the best he could think of to do. Perhaps if the Uchiha pride were to be bruised, it would be easier to loosen his tongue. “Your name is feared by many, but as I look at you, I only see someone who barely looks like he has eaten a good meal in many fortnights. Is it safe to assume you rely on your eyes to do the fighting that your body doesn’t seem capable of doing?”

The goading appeared to work somewhat, as the slight narrowing of eyes was the only give away that the words did annoy the Uchiha. It was not surprising, as Shikamaru was sure that being perceived as weak in the shinobi world was one of the most frustrating things one could be told. “For someone who looks as though he could pass out at any moment, are you really attempting to get some sort of rise out of me?” His words were laced in some amount of humor, as though the Nara heir was acting more endearing like a measly cat than a fearsome opponent. Even if he was not a fierce opponent, and that much Shikamaru was aware of, it still did not sting his own ego to know he was being looked down upon. It appeared his plotting to get any sort of slip of the tongue from the Uchiha would be far harder than he originally anticipated. Reserving himself to a sigh, he flinched as his slouched position paired with his deep breath only aggravated his wound more.

He reflexively flinched when an object came to land on his lap, and Shikamaru knew he was truly off his own game as he did not notice at first. Peering at the small tub, he considered what it could possibly be as his eyes went to gaze into those red depths. Honestly, it was weird considering that he did not feel as intimidated looking at the Sharingan the longer he was in the presence of the Uchiha. If he were not dead yet, that had to be a sign that looking into the missing-nin’s eyes would not sign away his life any faster. Evidently, he had a look of confusion upon his face as the other’s deep voice rang through the silent forest around them. “It’s a numbing salve, it will help you move easier and be more helpful than whatever you originally put on your injury.” Shikamaru knew that he could have packed his pouch more carefully, but realistically he didn’t think any rogue shinobi would attack him out of the blue, so he hadn’t put anything more helpful than a basic medical salve Ino gave him one time. He found that his guttural reaction was to say some sort of gratitude to the Uchiha, but he held his tongue as he wordlessly applied it to his wound.

Perhaps he was putting too much trust into the S-rank criminal, his mind whispered, but really, he did not see any other avenue that he could take. All he could do was be silently grateful when after he applied the ointment and reapplied the pressure from his makeshift gauze to the wound that he did feel the numbing agent taking effect. It was becoming easier to breathe, the expanding of his ribcage no longer perturbing the wound as much. Still, his mind knew that this was not right. That two enemies could not be this helpful to each other, that Itachi confessed he had no gain from helping Shikamaru. The entire life of the shinobi was to not trust those who were not one’s ally, and he knew for a fact that Itachi Uchiha was as far from his ally as they came. As he looked into those eyes that were rumored to speak of nothing but destruction and murder, he could not ascertain any sort of malice in them. If anything, he could only take note of the genuine exhaustion they held within them. It was as though the Uchiha had lost what it meant to fight, and he considered what the lack of the Akatsuki cloak could represent.

“Why are you out here? And don’t try to say that you are sitting by a fire and eating a meal. Were you sent out on a mission?” Shikamaru’s mouth opened before he really thought through it, and he was taken aback by how it did not seem accusatory. He was not asking the Uchiha for the reason of intel, he was just asking because he did not know what else to do. His mind refused his body to become too comfortable, knowing that partaking in a meal was one thing but succumbing to exhaustion was another beast entirely. At least if he held the semblance of a casual conversation he could focus on something other than the crackling fire or the crickets chirping off in the distance. It didn’t make sense that things felt almost calm, and if it were anyone other than Itachi before him, perhaps he would have let his guard down enough to actually find sleep. 

The missing-nin before him was unphased by the question, at least that was what Shikamaru presumed by the fact that he didn’t seem to bat an eyelash. “I’m not on a mission at the moment, I just simply wanted to leave to clear my mind for a few days. The forest has a familiarity to it, I’m sure that you understand.” It was true, the Nara could understand how the forestry of the Land of River could be taken for the forests of Konoha itself. Though, the trees weren’t as tall as they were in the Land of Fire, and the air was a tad more humid than the Nara would like, but as he gazed up into the night sky in the clearing they were in he considered if perhaps he could enjoy watching the clouds from there. Without the constant nagging and missions, just enjoying the nature around him. For a moment, he forgot where he even was, who he was even talking to, and as his head lazily moved to look back at the Uchiha he found that there was the beginning of a smile adorning the sharp features. 

“Yeah, I get it. Though, I doubt they enjoy you simply coming and going as you please. What if you were to, I don’t know, run into a Konoha shinobi?” And honestly, the lazy smirk that came to Shikamaru’s face had no right to be there. There was no reason why he should feel comfortable with the mysterious Itachi Uchiha who slaughtered his family in cold blood, but yet he was. It was tranquil to not have to be complained at or told what to do, a life outside of the shinobi world that told him what was and was not allowed. 

“You’re the one and only I have come across. Most shinobi don’t take this route to return to Konoha, and even if they did, they wouldn’t notice me unless I wanted them to.” 

Now that - those words - they did not make any sense to him. If Itachi was truly competent enough to hide his chakra signatures, how was it that Shikamaru felt him before he saw him? Did that entail he wanted the Nara to sense him, to know that his presence was close by? If that were true, then that would mean that Itachi sought this confrontation out, that he wanted to come to Shikamaru and help him. His mind struggled to focus on the weight of the words given to him as he was groggy and sleep deprived and fighting off death, but he would remember them. Shikamaru doubted he would not remember this encounter for weeks to come, haunted by the odd compassion that a murderer of his own clansmen held or the way that his eyes seemed to soften the longer they were together. If the Nara were a more naive man, perhaps he would have thought that the Uchiha was simply lonely. He nearly laughed at the thought of how ridiculous that idea was, and even if there was some truth, it was hardly as though the raven haired man did not bring it upon himself. Itachi Uchiha deserved to be lonely. 

Potentially, this was more dangerous than Shikamaru even originally realized. The lack of a response to his insinuation that the Akatsuki would not be appreciative of the Uchiha coming and going only made him ponder if they did not mind because he wasn’t very far. The Nara only knew of Kisame Hoshigaki, Itachi Uchiha, and Deidara of the Iwagakure. Sasori of Sunakure was also on the list, however, he was proclaimed dead by Sakura’s hand. There was no readily available information on who was confirmed to be a part of the S-rank missing-nin group, especially as Shikamaru was only a Chunin, and as such there was no telling who else was slinking through the Land of River. Perhaps they were also conveniently wondering around, waiting for their next prey to inflict unimaginable damage onto. The likelihood of Itachi giving up the whereabouts of the hideout was low, to the point where Shikamaru felt it was too troublesome to even bother asking. 

“For being a Konoha shinobi, you aren’t asking many questions that could help aid them in my defeat,” Itachi’s words weren’t as accusatory as they could have been, more akin to him simply pointing out what he has perceived himself. Shikamaru shifted to put his arms behind himself, leaning back and considering what the proper response to something like that could even be. Perhaps had it been anyone else he would have put on his normal lazy smirk, would have teased about it being far too troublesome to try to interrogate someone as closed off as the Uchiha. 

“I find no point in uselessly wasting my breath demanding questions that you won’t even reply to. There is also the likely chance if you are displeased with my prodding you could kill me before I even realized what had happened.” All that got him in retort was a hum of acknowledgement, as though Shikamaru could be correct in his assumption. The Nara didn’t know if that was comforting, to know the man before him was truly dangerous and well equipped to kill him despite his gaunt appearance. Looking toward those dangerous eyes once again, he considered just why the other was so sickly. His own brain was finding it hard to process all the information he was being given by just allowing to look at the shinobi before him, and he found that it was harder to keep from letting his tongue loosen.

“Are you ill?” Itachi seemed to pause his movements, almost stilling to the point where Shikamaru was unsure of if he was even breathing, and he wondered if the swirling of the Sharingan meant his untimely demise. The man before him had three tomoe within his reddened eyes, and Shikamaru found himself interested to learn what it meant. Before the massacre, little was known about the Uchihas sacred eyes, a clan secret through and through, so there was nothing that Shikamaru had to understand the complexities. It wasn’t until the other moved to grab his canteen from his side and pass it to the Nara that he even remembered that the Uchiha wasn’t just there to be marvelled at. Wordlessly, and with some embarrassment on Shikamaru’s part, he accepted the offering and took a drink of the water within the flask.

“You’re more perceptive than most Konoha shinobi,” and Shikamaru took that as a yes. That the man before him was ill, and perhaps it meant a death warrant for the man before him as well. How long had he been ill? Were there no medics within the missing-nin group to help heal him? All those were questions that Shikamaru felt were too personal, too invasive in a way that would make the Uchiha flee. The Nara pondered if he were not injured, would the interaction between the two of them remained the same? Certainly not, as Shikamaru would have fled the scene to report his sightings to the Hokage as soon as he was sure the Uchiha wasn’t on the hunt to intercept him. 

“The Nara clan raises only the finest,” Shikamaru almost ruefully retorted, feeling dead tired in a way that even the Sasuke retrieval mission had not managed. He could muse that he was fighting death, starting to consider if the gash was simply that. The knowledge of poisons being prevalent in the Land of Wind blooming into his mind and he considered if that was happening to him. His own knowledge was limited, and he considered if the next time he was in Suna if he should ask Kankuro to teach him. Perhaps he would not be stuck speaking with a missing-nin who was slowly becoming more humanized by the minute. Passing the canteen back to its owner, he wondered how someone could show compassion to an enemy.  _ Nothing to gain, nothing to lose _ rang through his mind almost mockingly.

“You have quite the trek back home, Nara-san,” Itachi spoke up after a moment or two of passing, and Shikamaru was taken aback by the honorific. If the hint of a smile was anything to go by, he supposed that the man before him found his shocked look to be humoring. “You should get some rest. If it will make you more comfortable, I can take my leave. Keep the salve with you, it will do you more good than I.” 

Shikamaru almost insisted that the other stay, for reasons unknown, but maybe it was due to the fact that he was worried he would not wake up. If it were poison that was slowly eating away at him, how would he survive the night alone? Instead, he knew he should take the other’s out and wordlessly nodded. It didn’t take but a mere second before the other dispersed into a flock of crows, gone as if he was never there to begin with. It was interesting, he decided, to know that he had a chance encounter with someone that he would likely never meet again. Still, there was the struggle of getting back home before his injury worsened. Deciding that was a problem for the morning, Shikamaru hastily meandered around his surroundings to place traps that would alert him of any unwanted guests while he slumbered. His mind mused that Itachi could probably disengage them all before he knew what happened, but it was still better to be safe. Taking to laying by the fire, facing toward it as to not aggravate his wound more than he already had, he allowed himself to succumb to the exhaustion his body felt. If his dreams were filled with blood red eyes, he would simply deny such a preposterous idea. 


	2. A Troublesome Dilemma

**Notes for the Chapter:**

> So, uh, a few weeks turned into a few months. Whoopsie.
> 
> Sorry for the delay, I hope you enjoy this chapter! Thank you all for your kind words and kudos, and sorry in advance that there is no Itachi in this chapter!

Shikamaru managed to return to his village, though it had taken far longer than he would have liked. His presumption that others would be lurking the forest in search of a fight were false, as he had not even sensed anyone else’s presence around him. Given, he had no true sensor abilities, but to his knowledge no one was awaiting in the shadows for him. He nearly cried tears of joy as he came to the Land of Fire territory, thankful to be home and far away from the desert. It was just before dust broke that he saw the gates of Konoha before him. Izumo and Kotetsu seemed alarmed at his presence, taking in his slightly paled form and imploring if he would like to be escorted to the hospital to be looked over. Sighing at the troublesome nature of being fussed over, no matter how minimal it may be, he simply shrugged off their offering and made his trek to the hospital on his own.

His mind still swirled with thoughts of the Uchiha, the mysterious and almost haunted aura Itachi managed to give off, and he was nearly driven mad by it. The entire way back to his village, he pondered if he would catch a glimpse of the man, but he did not see any sight of him. All that was around from time to time were the occasional crow. Shikamaru stilled by the gates of the hospital, the realization hitting him at Itachi’s disappearance that night. He had turned into a flock of crows. Was it a mere coincidence that a crow was also following him through his journey home? Sighing at his own ridiculous nature, he flinched at the wound by his side. It had only gotten worse, turning a worrying shade of red and throbbing even when he did put the numbing salve on it. The yellow discharge did not help ease his mind, and he was positive that he had gotten an infection.

That was when he nearly collided with Sakura, almost forgetting that the Chunin was even a part of the hospital staff. She seemed for a moment peeved that he even dared to stumble into her, the almost childish anger she had yet to let go of during their years as shinobi evident on her face. Belatedly, he realized that she was holding vials full of samples of some kind, and Shikamaru decided that perhaps he deserved her wrath. Before she could get a word out, she seemed to hesitate. “Shikamaru?” She questioned, almost as if she was as surprised to see him there as he was her. “You look terrible.” As much as he wanted to lazily blow her off and insist that he was not in as bad of a shape as he was; there was something about her gently putting the samples down on the counter of the nurses’ station and immediately leading him toward a room that filled him with warmth.

He was still exhausted, and under the impression that the Hokage was perhaps anxiously anticipating his return to the village. Even though he was only two days later than he wanted to be, Shikamaru was never one to take his time returning home. As he was told to sit on the bed and await a medic to come to him, he truly anticipated it would be just a nameless face. Perhaps it was silly of him to think that way, and he was starting to become frustrated that everything he thought seemed to be challenged recently. Lady Tsunade walked into the doorway with her eyes seeming to bulge slightly at his appearance. It had been awhile since he had seen himself, was it truly that harrowing of a sight? Shikamaru decided that the surprise was mainly due to the fact that his mission was supposed to be simple. That there was a low risk of him being injured, just as there was a low risk of him stumbling upon a lost Uchiha. 

“Hokage-sama,” was the greeting he gave to the woman, feeling too exhausted to be more cordial. Honestly, all he wanted to do was sleep for at least a week. 

“What happened? Show me your wound,” her voice was as hard as it usually was, attempting to conceal her own shock. Shikamaru did not argue, glad that the best medic in the Land of Fire was before him. Sliding off his flak jacket with some amount of difficulty, he took off the makeshift compression he made, flinching as it seemed to have attempted sticking to his side. It did not look any better than it had the last time he tentatively looked at it, showing signs of deep red as well as the oozing yellow discharge that was there since he had woken up after his encounter with the Uchiha. He could not smell any odor from it, however, so he supposed he should count himself lucky that his flesh did not appear to be rotting away. “Lay down,” Tsunade spoke again, this time a touch gentler as if she originally did not believe that he was as wounded as he made himself out to be. Perhaps there was a time before that he made his injury out to be worse just so that he would be allotted time off missions, but Shikamaru would vehemently deny that.

She seemed to be busy gathering supplies for herself, putting them into a large bowl. It seemed mostly liquid based, with medicines that he never took the time to learn about. Really, he never found himself much inclined to be in the hospital, finding his time better spent watching the clouds. “I was heading back from Suna, when rogue shinobi attacked. The pain has been getting worse progressively throughout my trek back to Konoha, but I haven’t had any major issues other than being weak on my feet and being feverish. I’m unaware of if their weapons were poisoned, but it is a possibility.” The movement of laying down only seemed to agitate the wound more, but he kept himself from showing it beyond a flinch. It was weird how his heart felt as if it was still racing out of his chest, and he had originally thought that it was because he was running on adrenaline, but even as Shikamaru laid on the bed it did not cease. 

His hands felt clammy as he wiped them on the bedsheet below him, and it was hard to not squirm due to the fire he felt on his side. His mind was so consumed with thoughts of getting home, that he hardly realized just how terrible he felt. A haze of exhaustion mixed with pain caused him to assess just how miraculous it was that he even managed to return to Konoha. Would it have even been possible if Itachi had not offered him the numbing salve? Could he truly have made it through that first night if his body was so consumed with the throbbing pain that seemed to radiate through his entire abdomen? The odds were low, and Shikamaru was left with only more questions on why his supposed enemy chose to aid him instead of finishing him off. Words were becoming harder to think about, but even if he was sound of mind he knew that there would be a hesitation to reveal his encounter with the Uchiha. It was as though simply being in the presence of the medical-nin paired with him finally being able to rest were causing the pain to reemerge tenfold. 

“There is a likely chance you were poisoned by the attack, but if you were, it is shocking that you still managed to get here without succumbing to the pain. The antidote I’m making will hopefully take out the toxins that are in your wound. My only concern is that it has spread far beyond just where you were injured,” she spoke as she used her chakra to collect the medicine into a ball. Shikamaru could only watch as she approached him, a look of concentration on her face as she hovered the ball close to the gash at his side. At first all he could feel was red hot pain that radiated throughout his entire body, letting out a small howl as he could feel the medicine pressing into his side. It almost hurt worse than the actual wound itself, his throat emitting grunts of pain as he had to physically stop himself from thrashing around. His hands gripped at the sheets below him, gritting his teeth as he watched Tsunade do her work.

Her able hands did not cease even with him writhing in pain, working to extract the inky traces of poison that were brought up by the antidote. Shikamaru did not know if he would be able to handle more of the pain, but it did not seem to matter as she seemed set on examining the rest of his body where the poison could lie. As she hovered the medicine throughout his body, he could only watch in slight disbelief as she managed to pull some out from his thoracic cavity. It appeared as soon as she had done it, that the clenching of his heart seemed to lessen, although it was beating equally as fast from the stress of the procedure. Letting out harsh breaths from his nose, he was simply glad that she seemed confident that the toxins were out of his body. Laying weakly against the bed below him, he found it nearly impossible not to succumb to the exhaustion he felt all throughout his body at that point.

After the antidote had been given throughout his body, he could only blearily watch as the Hokage’s hands worked dutifully to heal the opened wound. It was quite spectacular to watch how the woman’s chakra was able to aid in the healing, glad that he did not require stitches but in the back of his mind aware of the scar it would undoubtedly bring onto his flesh. Tsunade grabbed some gauze from the metal plate she had the bowl on, working to cover the injury. It was all troublesome, and Shikamaru knew he would not be as foolish not to prepare for the worst of any mission again. 

“You will stay here overnight to be monitored, and once you are released I expect a full report on what transpired,” Tsunade spoke, her voice softer than it normally was. Shikamaru only nodded at the request, finding sleep approaching him faster than he thought it would. The sound of her shoes walking out of the room was all he heard before the room was consumed in silence. His thoughts whirled around what his report would even cover. Certainly it would be suspicious of him to write in a report about Itachi Uchiha when he did not speak of it to the Hokage, but perhaps he could say he was so consumed with pain he let it slip his mind. Although, it was not a random man he encountered, but someone who was hunted by Konoha for years. Turning his head to gaze out the window of the hospital, Shikamaru knew that it was too late to share his information. He would simply not bring it up and be done with it. It was the least he could do for the one who saved him from dying in the Land of River. 

He had only wanted to watch the clouds before drifting off, had not thought he would be thrown for another loop. As his hazy eyes looked, however, he saw a crow sitting on the sill, its eyes peering directly at him. Shikamaru forgot how to breathe for a moment, lost in the eye contact with the bird as it stayed motionless. He was under the impression he was in some sort of delirium as he swore the crow held one red eye akin to Itachi’s own. The eye seemed much different, more angular and deadly than anything Shikamaru had ever come into contact with before. As soon as he managed to take note of such a thing, the bird flapped its small wings and took flight. Gone as if it had all been in his mind, and all Shikamaru could do was contemplate if it had even been there in the first place. There was no possible rhyme or reason for the Uchiha to keep watch over him was what he decided as he finally closed his eyes. His mind whispered that there was no rhyme or reason to Itachi’s entire being. 

Shikamaru managed to sleep through the night, finally able to relax due to his injury being tended to, and it was not long before he was released the next day. The nurse who discharged him told him that he was to take it easy the next week and not stress his injury, and all he could do was nod noncommittally. It would be easy for him to take it easy, and just as he was gathering himself to leave the room there was the overwhelming burden placed onto him that knew he was going to have to write a report soon. The longer he pushed it off could perhaps be chalked up to him just wanting to recuperate at home, but there was only so long before it seemed like he was hiding something. Shikamaru knew there was no feasible reason for anyone to suspect his hesitance as anything but laziness, yet his mind still told him that he was going to be found out. That before he knew it, Anbu would be escorting him to the Hokage’s office with words like treason or something equally as truthful. His actions spoke of nothing more than covering for the enemy. 

Walking through the streets of Konoha back to the Nara compound, albeit slower than even his normal casual stride, he still pondered over the encounter. Itachi Uchiha was a puzzle of a man, the kind of puzzle that concealed its secrets far too well, and Shikamaru had always been privy to such puzzles. That had to be why his mind was still obsessing over figuring out if his meeting was simply dumb luck or if it happened that something much more sinister was soon to divulge. Coincidences were hard to come by, and fate was a laughable matter to the young man, but yet both those things seemed to be the easiest way to explain the situation. Though it did beg the question of if Itachi had healed Konoha’s own before, if he felt some kinship towards the village he deserted. The village that both Uchiha brothers seemed to feel nothing but spite and indifference towards. Perhaps the most maddening part of the entire situation was that Shikamaru knew he could not simply ask anyone for details pertaining to the Uchihas. It would lead to too many questions about his own curiosity, and maybe the only one who would not ask any questions would be Naruto. Yet he doubted the Uzumaki had any viable information, as even if Sasuke and him were friends, the young Uchiha was much too secretive.

Finding his way into his home, ever grateful that it seemed as though his mother was out with friends so that he did not get nagged at for one thing or another, he took off his shoes and made his way into his bedroom. He found that he was not hungry, did not want to do anything but sleep, and yet his mind still reeled with what little information he knew. Itachi said he was tired, but what was he tired of? Was he tired of fighting or was he simply tired of existing? Was someone who was considered vile and evil even capable of feeling such emotions? Sprawling out on his mattress, he found himself more exhausted than he originally thought he would be after such a short walk. At times, Shikamaru wished there was a way to turn off his brain, to simply disengage and fly away on the clouds he always found himself envious of. To be without a bother in the world sounded much more compelling than to be consumed with an impossible puzzle.

His mind would be haunted by such a mysterious man for days to come, often preoccupied with his own thoughts to the point that all he would do was sit at his favorite spot and watch the clouds lazily pass by. The report he was to write left completed up to the point of the encounter with the Uchiha, where his pen refused to meet paper again. As if his writing of the account would make everything far more real than just a simple puzzle to him. Every time a bird would pass over, he would seek out the signs of a crow, but none would pass. It was as if his own imagination had conjured up a sharingan he had never seen himself before, but that was not right. Shikamaru knew himself to be many things, but verging on insanity was not one of them. Laying with his arms tucked behind his head, he knew what he saw was true, that even his mind could not conjure up someone he had never met in the first place. His vision was obscured by a shadow, causing him to look toward the source of his disturbance only to see Asuma’s own grin behind a cigarette.

“You’re looking more pensive than usual, Shikamaru,” the man’s words rang through his head as he took a seat beside the Chunin, letting out a billow of smoke as he stared towards the clouds himself. “I heard you were injured while on your last mission.”

Shikamaru let out a sigh as he wafted the air around him as smoke evaded. He truly wished his sensei would stop smoking those damned things. “Rogue ninjas were on the prowl, I was in the wrong place at the wrong time.” The Nara considered telling Asuma about everything, but he knew that it wouldn’t make sense if he spoke those words. It was likely that most would believe it impossible that Itachi Uchiha would save anyone, let alone a Konoha shinobi. As he peered at the older man, he found that he yearned for someone to tell him that he was not crazy, that it was justified that he felt some amount of curiosity toward the situation. 

“Luckily you made it back home in one piece,” Asuma concurred. For a moment they sat in silence, the Jounin taking long drags of his cigarette while Shikamaru debated if there was anything he could say that would make his thoughts actually sound unlike someone on the brink of insanity. Was it wrong to feel some amount of indebtment to the enemy? Would the feeling of curiosity vanish with the passage of time? Logically, he knew that he could push it towards the back of his mind and ignore all that had happened. He could put pen to paper and write as though he never met the Uchiha and move on, but there almost felt like something more would be to gain if he just pushed. If he could only prod and look into more of the facts as they would be presented to him if there was anyone he could ask. 

“You know, Shikamaru,” the other’s voice rang, causing him to avert his train of thought for the time being, “I can practically hear the gears turning in your head. What’s going on?” 

Shikamaru’s immediate reaction was to curse his sensei for understanding him so well, in knowing what the Nara was feeling with just a short amount of time spent together. For the most part, the young man knew how to conceal himself so that people never pressed or prodded at him. Surely in the past few days Shikaku had also realized that his son was lost in his own mind, but his father was the kind of man to not pry unless absolutely necessary. The Nara men had an understanding, the sort in which neither spoke of issues unless of utmost importance. Perhaps it was why Shikamaru looked more toward Asuma when it came to his own problems, the natural warmth that radiated off the man much preferred to the calculated and gruff nature of his own father. He knew rationally that he was allowed to not answer Asuma’s question, to brush it off and ask if they wanted to play shogi instead, but he supposed someone else’s insight could help ease his thoughts.

“What makes a shinobi good or bad?” Shikamaru’s words left his mouth before he could fully stop them. He knew that it didn’t sound one way or another, and he doubted it would make Asuma suspicious in any real way. They had countless talks about philosophy and morality, simply speaking of their own opinions on any matter that came to mind. 

Looking at the man, he saw Asuma’s own face turn to one of deep thought, pondering the question himself. Shikamaru knew he was skirting a dangerous line when it came to asking, putting a card down that could unravel his entire hand if he weren’t tactful in the situation. He had no reason to conceal his encounter with Itachi, and yet it had already happened, and it was going to continue at the rate he was going. Asuma pressed his cigarette against the wooden bench they were sat on, taking in a long breath before he spoke up once more.

“It’s how they act toward fellow shinobi and those they swear to protect,” a moment of pause was placed between the two of them before he elaborated, “if I were to turn my back on someone in danger or distress, then I would have no right to wear this headband. No matter how dangerous a situation may be, going out of your way to defend someone else and putting your own life on the line is how you know a good shinobi from a bad one. Someone who acts selfishly or without regard for their village would constitute as an inherently bad shinobi.”

It didn’t help Shikamaru’s turmoil at all, in fact, it made him more uncertain. If what Asuma said were the truth, then how could someone be both good and bad at the same time? Was there such a way to be both at the same time? Perhaps talking of only shinobi was the wrong way to approach it, perhaps it was better to be discussed on the scale of humanity as a whole. Letting out another sigh, trying to keep his uncertainty under tight wraps, he looked back toward the sky in an attempt to make the conversation easier.

“Could someone be both good and bad?”

“I suppose so. Everyone makes mistakes and fails occasionally. It’s a natural part of life. I think the most important part is that you don’t lose yourself in your mistakes, but you allow them to mold you to a path of betterment. We’re shinobi, sure, but that doesn’t mean we’re above failure or the need to improve ourselves.”

Could a mistake truly be assassinating one’s entire clan? It was almost comical to believe that such a thing could be something Itachi regretted, as it was such a heinous act. It spoke of someone who was bloodthirsty and ravenous for… His mind stilled for a moment. What could he be ravenous for in doing the acts that he did? Was it for power? Was it so that he could prove that he could do it? Why keep Sasuke alive, then? Shikamaru did not have any idea, did not even know where to begin seeking such answers. It was not as though he would ever find himself in the presence of the Uchiha again. Except, there was, was there not? He knew of where Itachi was stationed, at least around where he was. Though, it would be hard to believe that someone as secretive as the missing shinobi would be so ready to tell Shikamaru of something like that.

“I wouldn’t be so hard on yourself, Shikamaru,” Asuma said, taking his large hand and clapping Shikamaru’s shoulder with an easygoing smile on his face, “you’re a hardworking and intelligent shinobi. When I was your age, I was thinking the same things. You’ll always be a good man in my eyes, and I’m sure the entirety of Konoha would agree with me as well. Any mistakes you’ve made along the way should show you that you’ve grown, not make you think you are inherently bad. You can’t save everyone, but that doesn’t mean you shouldn’t try with all you got, right?”

For a moment, Shikamaru considered if Itachi needed to be saved. The look in the Uchiha’s tired eyes expressing someone who had despair written into their bones, so deep seeded he knew not if the missing shinobi had ever felt true happiness. It was not as though the Chunin could do anything, realistically, nothing other than try to formulate the reasoning behind the other’s emotions. As he laid with his teacher looking encouragingly at him, he found that he wanted to try. He wanted to see if he could solve the puzzle that was Itachi Uchiha, if he could bring the other out of the darkness that was evidently holding him hostage. It was the most idiotic plot he had ever thought of, and he was starting to feel as though he understood why Naruto held on to Sasuke. Even if it was just one meeting, there had to be more to what was going on that even Shikamaru did not understand.

“Come on, I really came to get you because Choji has decided that we are all long overdue for some barbeque. I might have told him I’d buy in passing the last time we spoke and now he’s going to make me broke,” Asuma said, his face slightly paling at the realization of what he had essentially done to himself. 

Shikamaru found a lazy smirk come onto his face, knowing that if nothing more he had his squad to fall back on. Even though Ino was the worst nagger in Konoha and Choji managed to weasel his way into making Shikamaru pay for their food more times than he’d like to admit, he was always going to be surrounded by people he loved. Asuma truly cemented their team when they were still genin, showing them the importance of finding family in those who one fought alongside on the battlefield. If nothing else, he could use Ino’s gossiping and Choji’s excitable talk of food as a distraction from his own thoughts. Standing up together as they walked toward the barbeque restaurant team ten frequented the most, Shikamaru knew that he would not give up as easily on Itachi as he originally thought. 

They shared a companionable silence as they walked, and Shikamaru was assured that Asuma believed that his words had helped. Which, perhaps they had, in the way that his words built Shikamaru’s fortification that he needed to figure out what was transpiring behind those mysterious red eyes. He could only hope that their next encounter was as civil as their last.

**Notes for the Chapter:**

> I think the hardest part of this chapter was knowing that I wanted Shikamaru to speak to either Shikaku or Asuma about what was going on. Obviously, he couldn't say much without giving away that he met with someone dangerous. This was a good compromise, I think.
> 
> The talk of morality is very interesting, especially in a world such as Naruto where violence is almost encouraged with all the children soldiers that they make and practically mass produce. Haha.
> 
> Anyways, I hope the dialogue didn't sound too stilted and that you enjoyed reading this! Look forward to more soon!


	3. A Shoji Challenge

**Summary for the Chapter:**

> Oh, uh, hey guys. Sooo, it's been a hot second, but when hasn't it been? New school year, holidays, my own birthday this past weekend have all combined to delay this. 
> 
> ALSO I failed to note something very important I want to have on public record. Shikamaru's age is 16 and Itachi's is 21, that makes this pretty creepy from a society standpoint. I want it to be known that no sexual content or sexual encounters will be had between these two characters until Shikamaru is of consenting age. Not even one flirt, one wink, or even the hint of sexualization of a minor.
> 
> I know that in Naruto, pretty much as soon as you become Chunin it suddenly is like you're mostly an adult, but for my own sanity I wanted it to be known that there is a reason the underage tag is not being used. 
> 
> With that said, thank you, I love you all, and I hope you enjoy my cluster fuck.

Shikamaru decided that he was as knuckleheaded as Naruto was, as he laid in the forest staring up at the clouds in the Land of River. Perhaps naivety better suited the idealistic nature of thinking he could easily persuade Itachi into giving him any sort of information into his inner workings. Still, as he made camp with a small tent and plenty of traps in case other shinobi were seeking a fight, he could not help the hopefulness that bubbled up inside of him. The trip to his location, and now camp, had been easy, a simple day trip to the familiar spot of that fated encounter. The clouds were just as peaceful there as he had imagined them to be, perhaps he had vaguely noticed their tranquility when he had awoken before his side had been tended to, but he couldn’t quite remember them being as such. Part of him wanted to float up into them while a majority of himself wanted to stay grounded, to understand the puzzle that he found himself stuck within.

It was nerve wracking to intentionally lie on his report, feeling as though he was doing a dishonor to his village, but his mind had long been made up that he could not bring anyone into his dilemma. Outwardly, the report seemed completely normal. Instead of putting his encounter with the Uchiha on paper, he wrote that he had managed to build himself a fire and used his own resources from his pouch to continue his way back home. No one seemed to bat an eyelash that the Nara would have prepared for a situation such as that, the heir known for his logical mind and quick thinking. Still, even though he had managed to get away with his small lie, hoping that it would not blow up in his face, he knew that he had to make his way back to the Land of River. Knowing he could not bring suspicion to himself, he instead decided that he would depart on the terms of the village.

Getting permission to leave the village had been harder than he would have liked, with Tsunade nagging at him that he should stay and relax for another week before straining himself. Naturally he had told her that he only wished to go to Sunagakure to learn of poisons from Kankuro. She did not seem fully convinced but there must have been a determination in his eyes that she had very rarely seen that allowed him to depart. No one questioned him for bringing more supplies than one would reasonably need for the short three day trip to the desert village, more than likely presuming he would be taking his time. That he would, Shikamaru had long decided, even bringing his own personal shogi board for plans that he hoped would come to fruition. Even as he had left, he heard the guards playfully tease that he was just going to Sunagakure so soon to see his girlfriend. He had to stop himself from bickering that they were wrong, knowing that the narrative that he could potentially be romantic with Temari would only help aid his disappearance.

All he could do once he made it to the clearing was wait. It was unknown how long he would have to wait, if the Uchiha was still even near the area, but his mind was still buzzing with potential outcomes. There was the chance that Itachi would not be pleased with his return, that he would attack Shikamaru on sight, and it could only end in untimely demise. Another route was that the mysterious man was long gone, having already been sent out on another mission the Akatsuki assigned him to, and Shikamaru was just wasting his time. The third and most appealing option would be the man even show up, perhaps humor the Nara in his idea and then… Well, there was no real telling what would transpire afterwards, but perhaps he would get that much closer to figuring at least something out. Naturally, he was not foolish enough to believe he would crack the code, not in the first meeting if it were to arrive, but even being able to peer into the pandora box was enough.

Having set up camp somewhere around noon, Shikamaru’s spirits felt disheartened at the acknowledgement it was nearly dusk and still not a sight of the Uchiha. With some amount of bitterness at knowing his plan was not going as he wished it would, he built a small fire in hopes the smoke would alert Itachi of his presence. He knew it would alert his presence to anyone nearby, but he did have a few ideas on how to take down those looking for a fight even if the shadows were slowly being enveloped by the setting sun. The half-baked plan to talk to Itachi was feeling more and more naive the longer he sat by the fire. It would not take long to simply travel to Suna just as he had told Tsunade he would, that he could pretend that this had been a lapse of judgement and carry on with his life. If he had told anyone else about what he was plotting, undoubtedly he would be called mad.

Just as he was about to abolish all ideas of what he was attempting to accomplish by setting up camp in the familiar surroundings, there was a flare of chakra to the left of him through the bushes. His first thought was to tense up, to be prepared for a fight as it was still unlikely that Itachi was the only Akatsuki that was lurking in the forest, however they were moving far too slow for Shikamaru’s mind to process them as a threat. Still, he was on alert as the presence only seemed to be aiming toward him as the sky was darkening to a deep amber. It wasn’t until he saw the inky black hair of the Uchiha that he felt some relief, attempting to convince himself it was simply due to not having to get into an unwanted confrontation with someone. His eyes glanced over the man, finding him once more without a cloak that signified Akatsuki loyalty, finding that he was appearing more harrowed than the previous encounter. Despite the questions he wanted to ask, Shikamaru took to laying on his back as he inspected the sky above them.

“Just as I thought, this is a good place to watch the clouds at,” his words came out far more casual than his nerves felt. All of his plotting and scheming had left him with the knowledge that their next encounter could potentially turn sour, into a fight that Shikamaru did not have any true confidence he could even win if initiated. Still, even with his nerves raging onward, he knew there was unbridled hope that things would turn to his favor. 

“I’m glad to see you have recovered,” the deep voice to his left spoke, and Shikamaru wished that the exhaustion in those words did not make his mind consider why Itachi did not try to help himself. The actions did not speak of a man power hungry and deranged.

Silence fell over them once again, much more comfortable than the last time by bounds, but yet the Nara had no way of reading the other. Itachi was far more closed off than most shinobi, whom Shikamaru felt could easily be understood and combat against. Perhaps it was the mystery surrounding the sharingan, where there were no true recordings of the power that was hidden in the blood reddened eyes. The mysterious Uchiha stayed standing at the edge of the clearing, almost as if he was questioning whether it was worth his time to stick around or perhaps trying to surmise what Shikamaru was plotting on doing by coming there once more. The true answer was that the young shinobi had no real reason to be there, no true reason to even want to figure out the mystery that was the Uchiha clan. 

“Do you play shogi?” The Nara questioned, going to sit up and rifle through his own bag he put beside him. Itachi made no movements to come closer, although he had not immediately left, so Shikamaru would accept his small victories. Certainly the situation was as odd to the rogue shinobi as it was to Shikamaru, even though he had concocted it. Procuring the shogi board from his pack, he went to work setting up the pieces with full intention of Itachi joining him. 

“You came all this way to play a game?” Itachi questioned, and Shikamaru had to settle the slight smugness he felt at the Uchiha already falling into his game. The older shinobi went to sit across the board from him, his eyes gleaming the same red from before, and Shikamaru considered if the sharingan was always activated. It seemed unlikely, knowing that he had watched Sasuke’s irises go from red to onyx black. 

“Also to look at the clouds,” Shikamaru lamely retorted before taking to staring subtly between the board and Itachi, “it’s simple. Every time I win a game, I get to ask you a question.” 

Itachi’s eyes almost seemed amused at the premise, which was much preferred to the potential of the man brushing him off. His face, however, did not give away any hint of a reaction, just those deadly eyes that Shikamaru found himself often looking into. Far more often than he should, for those eyes undoubtedly would have the ability to cause him more suffering than he ever could imagine. Certainly most knew not to look Itachi Uchiha in the eyes, perhaps that was the cause of his eyes seeming far more expressive than the rest of his sharp features, and yet Shikamaru was the fool who found it not as intimidating as it should be to gaze. It could be due to the fact that he had not been put under a genjutsu as powerful as the sharingan was rumored to be, had only seen it in the chunin exams when Sasuke had utilized it to predict movements. If his naivety would become his downfall, Shikamaru decided that he deserved it. 

“Bold of you to assume you’d win a match, Nara-san.”

“As it’s bold of you to assume you’ll only win.”

Shikamaru knew he had to put his all into playing as tedious as it may be. Playing between Asuma and his father were more casual, knowing how they played and being able to predict their movements, even if his father’s strategies seemed to only advance the older Shikamaru became. Upon first glance, it seemed that Itachi was set on playing defensively, moving his pieces in a way that spoke of someone who was more tactical. More often than not, the young shinobi also played a more defensive game, but he knew that he would not get far without taking chances. Their match lasted for quite some time, as if they were testing the limits of their own skill set, and it was just one lucky move that allotted Shikamaru the win that he craved. Itachi looked slightly impressed, as if it was a feat to defeat him, and perhaps it was due to the Uchiha never losing. 

Still, as he knew that he had won, the cacophony of questions ringing through his mind seemed to all pile upon each other. Shikamaru did not know what question rang imperative to ask first, if there was even a question that Itachi would give an answer to. The older man seemed patient, however, simply taking to glancing at the Nara. It made him ponder more, doubt that all of this was not just a ridiculous idea that would only end in him regretting this decision. 

“How old are you?” The question itself was innocent enough, one that most would not mind answering, and Shikamaru knew that it would aid in putting things into perspective. 

“Twenty-one.”

It caused Shikamaru to pause, his mind reeling. With that information, it would put him as four years older than Sasuke. Naturally, he presumed that Itachi was older than Sasuke, but he had thought that the man before him would have been at least an additional five years older. The Uchiha massacre had happened when the rookie nine were seven, putting Itachi’s age of the slaughter of his clan at eleven. That was almost unfathomable, nearly impossible, and it only caused more questions to blossom into Shikamaru’s head. Could an eleven year old, despite skill and intelligence, truly take down one of the most prominent clans in Konoha? 

Only once he looked at Itachi and saw that the other was watching him did he realize that he could not allow himself to be caught up on the small details. He would have time to think more thoroughly over the information he was given later, perhaps when he actually made it to Suna. So, he went to busying himself making up the board once again, even noticing that Itachi was putting his own pieces onto the board. As if the S-rank criminal actually was enjoying the companionship, actually was lonely and wanted to have company such as this. An utterly ridiculous thought, but Shikamaru enjoyed the fact that the Uchiha did not bother to fill the silence with useless conversation. 

The sound of the pieces being placed on the board made Shikamaru feel a bit more peace, as the sun was nearly set overhead and the cicadas were chirping around them. It seemed that Itachi had taken to playing more offensively, taunting the younger man with the knowledge that he knew multiple strategies. Unfortunately for the Uchiha, despite his rumored intellect, he did not have Shikaku Nara to show him how to defeat nearly any opponent. As the fire lit their game, providing them warmth in the cool spring breeze, Shikamaru was finding that he was enjoying himself. It was fun, even, and that was not right. He should not be playing shogi in the forests of the Land of River with his proposed enemy, but yet he could only wonder what being an enemy even meant at that point.

Shikamaru had solidified in his mind that he had a perfect defense, having two of Itachi’s pieces taken off the board and a tactful defense around his king. That was, of course, until the Uchiha had managed to skillfully take his king in less than two moves, causing Shikamaru’s eyes to widen in some amount of surprise. Naturally, Shikamaru had lost against his father before and even Asuma a time or two, but he was under the belief that his skills in the game were far more advanced than most. 

“What’s your name?” 

“I’m sorry?” Shikamaru could not help but retort, finding the question almost jarring. Was it Itachi’s attempt at learning more about Shikamaru? Perhaps this was the plan all along, to get familiar with a Konoha shinobi to do something nefarious? Glancing into Itachi’s deadly eyes, he could not see any maliciousness. Yet again, he supposed that a question such as his name was innocent enough, much like his previous inquiry. Clearing his throat to hide his own embarrassment in overreacting to such a simple question, he quickly added, “Shikamaru.”

Honestly, he had pretty much known of Itachi’s name long before he had ever seen his face, to the point that he forgot he never introduced himself. Not that he necessarily cared if the man knew who he was. If anything, his mind was convinced that this was simply a way for him to figure out a complex puzzle, there were no real emotions. It made this meeting feel more safe, as though Shikamaru was not about to sell his soul to a demon. As long as he resolved that there were no attachments, it would make his own given mission more bearable. After he ascertained the information from the Uchiha, then it would be time to formulate the next step. 

“It’s nice to meet you, Shikamaru.” It sounded too polite, as though Itachi was actually pleased to be in acquaintanceship, and all Shikamaru could do was hum a reply. 

The next game ended in Shikamaru winning, and he had watched more carefully to see what he was missing in the Uchiha’s strategy because it appeared the other could utilize many strategies only pros knew of. There were even moves played that the Nara heir had never seen before, wanted to implore about, but he knew he had to save his questions for important topics. Topics that related to figuring out about Itachi’s past. The delicacy of the situation, the knowledge that at any moment the man before him could simply decide to no longer humor him, made him give pause to vocalizing anything for the moment. Would it be better to simply push as far as he possibly could? Certainly not, as it would only lessen the chances of another opportunity to pursue such a situation again. 

“What’s your favorite food?” Shikamaru asked, letting out a small chuckle at the absurdity of his question.

“That’s a strange question to ask me,” Itachi remarked, although his eyes did give some way to some mirth, “however, since you asked, it’s dangos.”

“Never imagined someone as feared as you to have a sweet tooth.”

“There is a lot to the world that you have yet to learn, Shikamaru-san.”

It felt as though Itachi was giving him a hint, as though he were encouraging Shikamaru to continue to implore, to continue his search for the truth. He never expected the other to want to be discovered, to have his life figured out, and perhaps there was a chance that the Nara heir was reading the situation all wrong. With a shaky foundation to begin with and a plan that had no clear ending, it was possible that all the Uchiha wanted was to lull him into a false sense of security. To allow him to believe that he was making progress in figuring out the puzzle that seemed to grow more complex the longer he sat in front of the shogi board. His resolve did not waver, however, knowing that he would at least get some answers out of the man that was before him. Even vague answers would work to patch together some sort of timeline within Shikamaru’s mind.

The next few games ended with the both of them asking vapid questions that held no true meaning. Questions that were mostly filler, evidently the Uchiha had no real reason in asking Shikamaru anything important. Perhaps if Shikamaru was not viewing the situation as his own personal mission, he would have believed that they were casually getting to know each other, but that was utterly ridiculous to even contemplate. It was growing obvious to the chunin that Itachi was growing tired, as his gameplay was turning more reckless as if he just wanted it to end, and Shikamaru considered if that was metaphorical in a melancholic sense. Still, at Shikamaru’s victory, the younger man offered one last question, resigning that it was enough for the night. 

“How long have you been ill for?” 

Itachi paused at that question, his eyes meeting Shikamaru’s own, and the Nara considered how many men had fallen dead where they stood willingly staring into those eyes. For a moment, it seemed that the Uchiha was considering his options, considering which route to take in the form of an answer. One normally did not openly express their own weaknesses, and despite his gaunt appearance, even the first night Shikamaru had met the man, Itachi had not admitted to being sickly. The question itself could be seen as a way to gather intel over the man’s weakened state, to reveal to Konoha that the dangerous Uchiha was perhaps able to be defeated, and if Shikamaru had just been upfront with his encounter to the Hokage then perhaps that would be what he was doing. Yet, there felt like too many variables and hidden pieces were just out of reach, to the point that Shikamaru did not want anyone else to be aware of the man and their haphazardous companionship. 

“For quite some time. I don’t know how long,” the other admitted after a long silence between the two. 

“Have you tried being healed?” Shikamaru knew that his question could have been ignored, as he asked without the shoji board being utilized, and Itachi had every right not to answer him. It was teetering on too personal, especially as the Nara heir felt invested in getting the answer. He rationalized getting emotionally attached to this man would end in nothing but anguish, and yet Shikamaru felt compassion. The kind of compassion he felt for his comrades when he went on missions, when he walked around his village. With the knowledge that by getting to know Itachi he found that the man was not the villain everyone painted him to be, was it wrong to perceive the man as something to feel compassion for? Perhaps it was just pity that Shikamaru felt, knowing that there was a man accused of crimes that seemed impossible for an eleven year old to commit. It was almost as though Itachi’s life was simply a series of unfortunate events.

“Most healers do not want to use their skill on rogue shinobi. Even those who do attempt healing can only help the swelling and superficial complications of my disease.” 

“Do you know what afflicts you?” 

“Respiratory disease, no one I have come into contact with knows what causes it or how to treat it. All I can do is wait until it consumes me.”

Shikamaru felt unnerved by the blasé tone Itachi used when talking about his illness, the pure disregard that the man held for his own health showed signs of someone who truly no longer cared. If that were the case, why still remain a formidable shinobi in an organization that was only known to cause misfortune and harm? The Akatsuki did not seem like it fit the other, his appearance gaunt and nowhere near as threatening as Konoha’s own shinobi seemed to swear it was. Never before had the Chunin encountered someone so ready to die, it was always quite the opposite, always a man at the brink of death who had no regard because his thoughts were consumed with victory. Defeat was not a part of the shinobi way. 

“Do you want to die?” Shikamaru’s voice was soft, barely audible over the crackling of the fire to the side of them. As soon as the words fled from his mouth, he considered if he even wanted to know the answer to the question. 

“My time will come soon enough, then I can get some much needed rest,” Itachi’s voice resounded in the unnaturally still forest, and there was a soft smile stretched upon his features that felt resigned to Shikamaru. It pained the heir to witness it, to see someone so resigned to death when there were potential ways to aid him, to help him if he just tried harder. 

Despite the lack of a concrete answer, Shikamaru knew the truth, he could see it in the way that the smile spread across pale flesh did not meet his eyes. It was then that solidified in his mind that Itachi was not a threat, at least not when they were placed in front of the shoji board as they were, for how could someone so utterly defeated be lethal? If it were still a game to gain intel or access into Konoha, which was a lingering possibility, there would be other ways that would still keep Shikamaru viewing him as a deadly being. Someone who was strong enough to take him down with one look. Perhaps it was still true, as he doubted that the other’s eyes were afflicted by the respiratory disease taking over the missing shinobi. Wordlessly, because Shikamaru was at a genuine loss for words for once in his life, he went to put up the shoji board back into his pack. He took his time, knowing there was nothing he could say in retort to Itachi’s declaration of resignation, yet he still did not want the other to leave.

“It probably sounds like I want to jump off a tall mountain, does it not?” Itachi’s voice rang, nearly startling Shikamaru as he looked over toward the other with slightly bulged eyes. “Don’t misunderstand, Shikamaru-san, there are many reasons the world is how it is. We’re all destined to die, we all will die, and in this world we live in that is filled with violence and death; the end is inevitable. The sooner we find peace and acceptance in death, the sooner we can find what fate has in store for us.”

“I think fate has nothing to do with living as we are now,” Shikamaru countered after a moment of pause, “for what even is fate? Who decides what is fate and what is simply a pure inconvenience? Is it fate that determines when I stub my toe or when I get a cold? Is fate that inherently detailed that it maps out our entire lives? We can’t simply live for fate, we need to carve our own way in this world or else we will be left behind.”

At those words, Itachi’s eyes finally seemed to light up, as if Shikamaru had unlocked the man to actively emote. The Uchiha’s laugh was filled with glee, a short chuckle that was cut off short by a wet cough. Without thought, Shikamaru reached toward the other to place a reassuring hand on his arm, but it paused midway as the older man seemed to compose himself. Itachi still allowed a smile to cross his face, this one much more organic and made him almost appear regal in a way. 

“You intrigue me.”

Shikamaru had no idea how to process that, to know if the other meant it in a positive or negative light. Despite the apparent disposition Itachi put on, he knew not how well the other was at masking his own thoughts or feelings. It seemed even more unlikely that Itachi Uchiha even cared about someone as insignificant as him, someone who was valued for his brains but not for any real physical attributes. Shikamaru was not the strongest, was nowhere close to being the strongest, so it seemed nearly unfathomable that someone as strong and dangerous as Itachi truly found interest. After another moment of silence, the Chunin found himself wondering the same question he had wondered when he first met the mystery before him.

“Does the Akatsuki not care that you are out on your own? I was under the impression that you all had partners.”

“I do, but we have come to an agreement. As long as we find each other again before the next meeting, we do occasionally part ways. We’re both pretty solitary.”

“For someone who is solitary, you are spending time with your assumed enemy.”

“Reality is how you perceive it. If I do not view you as an enemy, there is no reason to think of me spending time with you as such.”

“What a roundabout way to say you enjoy my company.”

It seemed they actually managed to joke around, as Shikamaru could not help but let out a laugh himself. The entire situation was ridiculous, everything that was going on in his life seemed almost like a fever dream, and he considered if his mind was just going insane. However, Itachi’s own laugh accompanied his own shortly after made Shikamaru realize the gravity of his situation. It was impossible to deny the camaraderie that was blossoming between the two of them. Even worse, as the night turned later and he found himself speaking more of philosophies and life with Itachi, he found himself enjoying the other. There were no labels to who they were when they were in the depths of the forest, hidden from the prying eyes of shinobi, they were just themselves. Shikamaru had no idea how refreshing it would feel, how amazing it was to know that someone saw him as something more than just the Nara heir. 

Shikamaru did not have any idea when his eyes became so heavy they closed on their own, had no idea when he fell asleep. All he knew was that when he woke up the sun was just peering over the horizon. Rubbing the sleep out of his eyes, he realized that his head was supported by the pillow he had packed, but had no recollection of grabbing it out for the night. As he turned his head to the side to investigate further, he found Itachi’s own form evidently dozing as he slumped against a tree trunk. Once again, Shikamaru had no idea what to say or do, but he did find some pride in knowing that the Uchiha let his guard down in front of him.

**Author's Note:**

> Hope you enjoyed the chapter! More to come in the upcoming days/weeks!


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